HCID 18918301, compound → Ethyl 3-(4-hydroxyphenoxy)butyrate

HRID 864863Notes

Reaction equation

HRID 864863 reaction equation
C([O:8][C:9]1[CH:23]=[CH:22][C:12]([O:13][CH:14]([CH3:21])[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:11][CH:10]=1)C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([O:13][CH:14]([CH3:21])[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:22][CH:23]=1

Participants

5

Reactant 2

HCID 18918301HCID 18918301, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18918541Ethyl 3-(4-hydroxyphenoxy)butyrateYield 93.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of the product of step (i) (4.5 g) in absolute ethanol (200 ml) was added 10% palladium-on-charcoal catalyst (1.2 g) and the resulting suspension hydrogenated at ambient temperature and pressure until uptake of hydrogen ceased. The catalyst was removed by filtration through celite and the filtrate was concentrated in vacuo to give ethyl 3-(4-hydroxyphenoxy)butyrate as a low-melting crystalline solid (3.0 g) NMR (d6DMSO): δ1.25 (3H,t); 1.8-2.0 (2H,m); 2.5 (2H,t); 3.9 (2H,t); 4.1 (2H,q); 6.7 (4H,m); 8.8 (1H,br.s); m/e 224 (M)+.

Workup

  1. customhydrogenated at ambient temperature
  2. customThe catalyst was removed by filtration through celite
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-e22b9a3e3f6e40e198ef5a229e9e4fa1
Source dataset
uspto-grants-1996_10
Patent number
US05563141

Reaction notes

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